Fluorescent and redox tetrazine films by host-guest immobilization of tetrazine derivatives within poly(pyrrole-β-cyclodextrin) films

被引:7
作者
Fritea, Luminita [1 ,2 ,3 ]
Gorgy, Karine [1 ]
Le Goff, Alan [1 ]
Audebert, Pierre [4 ]
Galmiche, Laurent [4 ]
Sandulescu, Robert [2 ]
Cosnier, Serge [1 ]
机构
[1] Univ Grenoble Alpes, Dept Chim Mol, CNRS, UMR 5250, 570 Rue Chim,CS 40700, F-38058 Grenoble 9, France
[2] Iuliu Hatieganu Univ Med & Pharm, Dept Analyt Chem, 4 Pasteur, Cluj Napoca 400349, Romania
[3] Univ Oradea, Fac Med and Pharm, Preclin Disciplines Dept, 1 Decembrie St, Oradea 410073, Romania
[4] Ecole Normale Super, PPSM, UMR 8531, 61 Ave Pt Wilson, F-94235 Cachan, France
关键词
Tetrazines; Polypyrrole; beta-Cyclodextrin; Electropolymerisation; Inclusion complexes; Biosensor; INCLUSION COMPLEXES; CARBON NANOTUBES; 4-AMINO-1,8-NAPHTHALIMIDES; ELECTROCHEMISTRY; CYCLODEXTRINS; MODULATION; MOLECULES;
D O I
10.1016/j.jelechem.2016.07.010
中图分类号
O65 [分析化学];
学科分类号
070302 ; 081704 ;
摘要
Tetrazines were immobilized onto electrogenerated films of polypyrrole functionalized with beta-cyclodextrin. Their immobilization was ascribed to the formation of the inclusion complexes between the tetrazines derivatives and the beta-cyclodextrin cavity. We proved that the resulting supramolecular material kept the electrochemical and fluorescent properties of tetrazines. This original architecture was used with success as a "bridge" to immobilize the beta-cyclodextrin-tagged glucose oxidase, chosen as an enzyme model, to prove the efficiency of the method to build new supra-biomolecular architectures. (C) 2016 Elsevier B.V. All rights reserved.
引用
收藏
页码:36 / 40
页数:5
相关论文
共 17 条
[1]   Synthesis and properties of new tetrazines substituted by heteroatoms:: Towards the world's smallest organic fluorophores [J].
Audebert, P ;
Miomandre, F ;
Clavier, G ;
Vernières, MC ;
Badré, S ;
Méallet-Renault, R .
CHEMISTRY-A EUROPEAN JOURNAL, 2005, 11 (19) :5667-5673
[2]   Cyclic voltammetric and scanning electrochemical microscopic study of thiolated β-cyclodextrin adsorbed on a gold [J].
Bollo, S ;
Yáñez, C ;
Sturm, J ;
Núñez-Vergara, L ;
Squella, JA .
LANGMUIR, 2003, 19 (08) :3365-3370
[3]   Inclusion complexes of cyclodextrins with 4-amino-1,8-naphthalimides [J].
Campos, IB ;
Brochsztain, S .
JOURNAL OF INCLUSION PHENOMENA AND MACROCYCLIC CHEMISTRY, 2002, 44 (1-4) :207-211
[4]   s-Tetrazines as Building Blocks for New Functional Molecules and Molecular Materials [J].
Clavier, Gilles ;
Audebert, Pierre .
CHEMICAL REVIEWS, 2010, 110 (06) :3299-3314
[5]   First Occurrence of Tetrazines in Aqueous Solution: Electrochemistry and Fluorescence [J].
Fritea, Luminita ;
Audebert, Pierre ;
Galmiche, Laurent ;
Gorgy, Karine ;
Le Goff, Alan ;
Villalonga, Reynaldo ;
Sandulescu, Robert ;
Cosnier, Serge .
CHEMPHYSCHEM, 2015, 16 (17) :3695-3699
[6]   Design of a reduced-graphene-oxide composite electrode from an electropolymerizable graphene aqueous dispersion using a cyclodextrin-pyrrole monomer. Application to dopamine biosensing [J].
Fritea, Luminita ;
Le Goff, Alan ;
Putaux, Jean-Luc ;
Tertis, Mihaela ;
Cristea, Cecilia ;
Sandulescu, Robert ;
Cosnier, Serge .
ELECTROCHIMICA ACTA, 2015, 178 :108-112
[7]   Inclusion complexes of cyclodextrins with 4-amino-1,8-naphthalimides (part 2) [J].
Goncalves Silva, Barbara Perez ;
Marcon, Rodrigo Oliveira ;
Brochsztain, Sergio .
JOURNAL OF INCLUSION PHENOMENA AND MACROCYCLIC CHEMISTRY, 2010, 68 (3-4) :313-322
[8]   Adamantane/β-cyclodextrin affinity biosensors based on single-walled carbon nanotubes [J].
Holzinger, Michael ;
Bouffier, Laurent ;
Vilialonga, Reynaldo ;
Cosnier, Serge .
BIOSENSORS & BIOELECTRONICS, 2009, 24 (05) :1128-1134
[9]   New tetrazine-based fluoroelectrochromic window; modulation of the fluorescence through applied potential [J].
Kim, Yuna ;
Kim, Eunkyoung ;
Clavier, Gilles ;
Audebert, Pierre .
CHEMICAL COMMUNICATIONS, 2006, (34) :3612-3614
[10]   Tetrazine-based electrofluorochromic windows: Modulation of the fluorescence through applied potential [J].
Kim, Yuna ;
Do, Jaekwon ;
Kim, Eunkyoung ;
Clavier, Gilles ;
Galmiche, Laurent ;
Audebert, Pierre .
JOURNAL OF ELECTROANALYTICAL CHEMISTRY, 2009, 632 (1-2) :201-205